


I Dare You

by chiefharbour



Category: Stranger Things (TV 2016)
Genre: Daddy Kink, F/M, Loss of Virginity, Smut, Vaginal Fingering, Vaginal Sex, Virginity
Language: English
Status: Completed
Published: 2019-11-26
Updated: 2019-11-26
Packaged: 2021-02-26 03:06:58
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,660
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21566587
Author URL: https://archiveofourown.org/users/chiefharbour/pseuds/chiefharbour
Summary: Prompt: First Time | After playing a small game of Truth or Dare with Hopper, your sleepover turns into a night you'll never forget.
Relationships: Jim "Chief" Hopper & Reader, Jim "Chief" Hopper & You, Jim "Chief" Hopper/Original Female Character(s), Jim "Chief" Hopper/You
Comments: 5
Kudos: 115





	I Dare You

**Author's Note:**

> I have re-written this prompt three times, and I finally decided on this idea over the others. Though one of them I was really akin to, I just feel like this one will resonate a little bit better with the majority of people who read these. But hey! If you think you’d like to read 18 y/o reader with Hop, let a girl know. Anyways, this one is a little bit more the speed I’m used to. Thanks to all of you for your patience! More coming on the way!

Grabbing your purse off of the console, you delicately balanced a large pizza box and six-pack of PBRs before shutting the door of your white corvette with your foot. You had managed to escape the hectic environment of the restaurant for the first time in weeks, and you had thought of no better way to spend your night off than with your close friend, Hopper. Luckily, the chief was able to head home early today as all of his cases were pretty much one-and-done. Eleven was sleeping over at Max’s house this weekend, so you knew that Hopper would appreciate any company he could get, especially when that company was his best friend.

Balancing the arrangement in your right hand, you knocked very carefully on the door to the cabin. Within seconds, Hopper appeared with a giddy smile and excitement rolling off of him in waves. He took the six-pack off your hands, giving your arms a little bit of slack.

“You are an absolute goddess,” he beamed, ushering you into his cabin before heading to the kitchen to put the beers in the freezer for a quick cool-down.

Following him after shutting the door, you set the obnoxiously-sized pizza box on the coffee table. Standing up, you shivered lightly from the chilly air of the wooden home, instantly regretting your decision to wear shorts and a tank top for tonight.

“Well, I hope you like extra cheese, because that pie is loaded,” you said, walking up to the bar separating the kitchen and make-shift dining room and straddling one of the bar stools.

He looked up at you with dopey eyes, “You are literally the perfect woman. How has no man snatched you up yet?”

You rolled your eyes at him, ignoring the intense swarm of butterflies that were being unleashed into your stomach, “Just because you butter me, it doesn’t mean you’re stealing any of my pizza slices.”

He chuckled lowly before bending over to grab some parmesan cheese from the refrigerator, giving you a nice look at his round and plump ass hiding behind dark-wash denim jeans. Biting your lip, you couldn’t manage to tear your eyes away from the sight.

Ever since you and Hopper starting your friendship a little under a year ago, your tiny crush on the man only grew. You tried everything that you could think of to forget about him, but your options were limited when it came to dating. Each time that the two of you hung out, you only became closer as friends; you desire, however, grew more and more. At this point, you had just about given up hope on ever getting with the older man. At twenty-five years old, you had now started to truly believe that your virgin-status was going to become permanent.

Hearing a gruff clearing of a throat, you shook your head out of your thoughts, realizing that you had just been caught staring at your friend’s ass for god-knows-how-long.

Cheeks blushing red, you tried to avert your eyes as he said smugly, “You know-I usually don’t mind pretty little things checking out my ass, but they usually act coy when I catch them in the act.”

You chucked nervously, walking back to the couch, “You wish, chief. I just couldn’t help but get distracted by your open fly.”

His eyes set in a panic as he looked down quickly, causing you to let out an embarrassing laugh, “Relax, asshole, I’m just fucking with you.”

“Wow,” he said sarcastically, dragging out the word. He joined you on the couch before opening up the pizza box, immediately claiming his side with a sprinkle of cheese. “So, what is the plan for the evening?”

You clapped excitedly before going for your purse and pulling out a VHS copy of _Alien_ , “I present to you the Ridley Scott classic sci-fi thriller. You game?”

He chuckled as he started to eat the first slice of pizza, “Doesn’t seem like I have much of a choice, darling, with you all excited like that.”

“Smart man,” you said, nodding your head before turning around, bending to set up the movie, unintentionally giving Hopper the best view of your ass. After hitting the play button, you turned around and caught Hopper’s eyes trained on your short-clad ass. Your heats turned a shade of rosy pink before he coughed, pretending to be letting his eyes roam all over the cabin. Biting your lip, you plopped down next to him, grabbing your own slice before allowing yourself to get closer to the warmth of his body.

About one hour into the movie, and one whole pizza and six-pack of beer later, the two of you had found yourself now sitting on the hardwood floor sharing a pack of Donettes and a bottle of Hopper’s favorite bourbon. The two of you had felt pleasantly tipsy and were exchanging wild stories from a time before you both knew each other.

“And I _swear_ , (Y/N), I almost snapped the bastard’s neck in half after that,” he said, powdered sugar all over the man’s mustache.

Giggling, you bent over and brushed the sugar off of his facial hair, “Wow, Jim. _What a badass_.”

“Better believe it, baby,” he said, sending a spark of pleasure to your stomach. You loved when he called you that; it made you feel safe and turned-on at the same time.

You chuckled, pushing his shoulder harshly, “Dumbass.” 

He smiled at you, a twinkle in his deep-blue eyes. You felt heat rise to your cheeks and nerves flutter in your stomach. Clearing your throat, you looked away, “I have an idea.”

“Oh, well, those are never good,” he said, taking a sip of his bourbon.

“No sleep-over is every complete without a good game of Truth or Dare,” you said, waggling your eyebrows suggestively.

He bit back the slight burn of the bourbon before looking at you with dubious eyes, “What are we? _Twelve_?”

“Ten, actually,” you bit back, stretching your legs out so they stretched across the man’s thighs. “Come on! You chicken?

“Oh, no, missy,” he said, looking at you with challenging eyes. “I am all man, darling. No chicken in sight.

_Oh, believe me. I know you are._

“W-What?” he asked, his own cheeks turning red.

_Shit, did I say that out loud?_

“I-um, was being sarcastic,” you said quickly, cursing yourself for your lapse in censorship.

“Okay, then,” he said, relaxing his back against the edge of the couch. “You start. Truth or dare?”

“Dare,” you said, acting very proud of your confidence on the first round.

“I. Dare. You.” he said, accentuating each word with a playful poke against your thigh, “To shove as many Donettes in your mouth as possible.”

“Oh, you are so on,” you said, sitting up and grabbing the bag of pastries before placing what seemed like an endless amount inside of your mouth. After you reached seven, you raised your hands in surrender, quickly spitting them up in a napkin close by.

“Damn,” he said, mildly impressed. “I always knew you had a big mouth, but I really had no idea.”

Laughing, you pushed his shoulder, “Shut up. Now, your turn. Truth or dare?”

“Hmm,” he thought, playing with his beard. “Truth.”

Raking your brain for a ridiculous scenario, you smiled when you figured out the most outrageous one, “Velma from _Scooby Doo_ , Betty Rubble from _The Flintstones_ , and Smurfette from _The Smurfs_. You have to fuck one, marry one, and kill one. Choose wisely.”

He laughed, tracing his mustache in concentration. “I would fuck Betty, marry Velma, and kill Smurfette.”

“Ah, a man of good tastes,” you said, nodding your head before taking a sip of bourbon. “Always marry a woman of culture and class.”

“What can I say?” he said, folding his arms behind his head smugly. “I have quite the thing for nerdy girls.”

With all of the conversations the two of you had shared about pop culture and your history of being a geek in high school, you couldn’t help from blushing furiously under his gaze, trying your best to not think too much into the offhand comment he just made.

“Alright, princess. Pick your poison.”

“Truth,” you said, resting your head against the edge of the sofa.

“Where was the craziest place you’ve fucked?”

You froze, mind going blank in search of an answer, _any answer_ , other than the truth. Should you tell him the truth? There was no point in hiding it; you were friends, after all. But there was a small part of you that didn’t want to embarrass yourself in front of him. You didn’t want to look so inexperienced to him.

“Well?” he said with knowing eyes, feeling successful in trying to stump you.

“Um,” you said, looking down at the floor and fiddling with the loose string on your shorts. “I’ve actually never, um-I’m a virgin.”

He looked at you unbelieving, his lips parts slightly as he waited for the punch line of the joke. Once he realized that there was none, he shook his head slowly, squinting his eyes, “You’ve never had sex before?”

Appearing uncomfortable under his intense stare, you shifted yourself to face away from him slightly, “I mean, I’ve made out with guys before, but we never really moved past second base.”

“Why?” he asked, tilting his head, suddenly more curious about another part of your history he had never known before.

“I always wanted my first time to be with someone I felt comfortable around,” you said, shrugging. “I’ve dated around, but I never really had a boyfriend. It just never happened, I guess.”

“Do you...want to?” he asked, turning his body towards your own. “Have sex, I mean.”

“I mean, yeah,” you said with a breathless laugh, looking at his face. You placed your hand closer to his own before looking down at the space between your fingers. “There’s this guy that I really like. I don’t think he feels the same way about me, but he would be the person I would want to lose my virginity with.”

You looked back up at him and saw a mixture of emotions in his eyes: confusion, disappointment, curiosity, and maybe... _lust_?

“Do I know him?” he said, biting the inside of his cheek as his fingers tapped idly.

“Yeah,” you said breathlessly. Your eyes scanned over the features of his face, your heart beating wildly. “I just think...I don’t know. I think he may think that I’m too young or silly or-“

“(Y/N),” he said, closing the space between your fingers and interlacing them gently. “You are the most gorgeous and sexiest woman I have ever met. If this guy doesn’t want to get with you, then he’s a fucking idiot and, quite frankly, you could do a lot better.”

Your jaw dropped slightly, your mind running in absolute circles. Your heartbeart picked up its pace in your chest and your breathing starting to quicken. You broke eye contact, pulling your hand away from his before grabbing the almost-empy bottle of bourbon and downing the remaining liquid quickly.

“Okay,” you hissed, placing the empty glass bottle back on the table. “It’s your turn.”

“Dare,” he said, eyes still trained on your face.

Swallowing loudly, you looked around the room for inspiration, “I-I dare you to, um...”

You looked at him and your eyes found the small part of his upper chest revealed by the first three buttons of his shirt, “... _take off your shirt_.”

His eyes widened in surprise. With a nervous laugh, he began to unfasten the remaining buttons on his scarlet-red flannel shirt. Maybe you should have dared him to eat some random food in his refrigerator, but, for some reason, all you wanted was to see the man’s bare chest. As eat button came undone, you felt more and more heat pool at your center, wanting nothing more than to kiss down his exposed chest.

After the last button was released, he peeled off his shirt and tossed it towards the kitchen, turning his head to look at you with a smug grin. You allowed your eyes to scan down his exposed chest, breath hitching in your throat when you saw how hard his nipples were getting against the cold air of the cabin. You felt your mouth salivate, wanting so desperately to trace your hand through his chest hair and down his stomach. You brought your eyes back to his, which were now clouded with lust. You felt your breathing pick up before you squeaked out, “Truth.”

He slowly brought his face towards your own, looking down at your lips before whispering, “Do you want to fuck me?”

Sucking in a large breath, you let out a whimper through parted lips. Looking down at his mouth and inching your face closer to his, your noses touching lightly, you breathed out, “ _Yes_.”

Not even one second later, the man had latched his lips on yours in a passionate kiss, his strong hands reaching up to cup your face in his hands, taking control. His mustache rubbed against your upper lip, leaving a pleasurable burn in its wake. His tongue grazed your bottom lip, prompting you to part your mouth and meet his tongue with yours. You released a loud moan, placing your hands on the man’s chest. Spreading your thighs, you wordlessly invited him to crawl over you and lie in between them. Pressing his hands against the couch on either side of your head, he began to suckle his way down your neck, his facial hair rubbing deliciously against your pale skin.

He sat back on his knees, trailing his hands down your sides before hooking his fingers under the hem of your tank top, pushing it up slowly as he stared into your eyes, licking his lips in anticipation. After removing your shirt, his eyes fell to your clothed breasts, your hardened nipples showing through the thin silk fabric of your bra.

He sucked in a breath before hunching over, latching his mouth to your left breast and massaging the right with his calloused hand. Whining loudly, you squeezed your thighs tightly around his waist, rubbing your center against the growing bulge in his jeans.

It wasn’t like you had never been touched before. You had found solace in self-pleasure soon after you went through puberty, so you were no stranger to the delicious friction against your sex. But, something about being pinned underneath the man you had been pining after for the better part of a year made you wetter than you had ever been before.

“Jim,” you whimpered, squeezing your hands on his shoulders, prompting his eyes to find yours. “I-I want you. I want you to be my first, if that’s okay.”

He chuckled low in his throat, the vibrations shooting down your body, “Baby girl, that is _more_ than okay.”

You had to bite the inside of your cheek when you heard the pet name roll off of his tongue. You would never admit it out loud, but you had had several wet dreams of the man currently above you calling you _baby_. In response, you never hesitated to call him _daddy_ , discovering a kink of yours that laid innate inside of you, ready to erupt at any moment. Every time you had seen the man in compromising positions or in tight clothes, it took all of your power not to whimper out the D-word, not wanting to embarrass yourself in front of him.

He stood up, bringing you up with him. He grabbed your hips and pressed his hardening member hard against your lower stomach. You shivered, mind suddenly reeling at the thought that you were about to see your incredibly sexy best friend completely naked. You froze, breath stopping as you realized that Hopper was about to be the first man to ever see you unclothed.

Noticing your distress, he bowed his head down to meet your eyes, “Hey, hey...we don’t have to do this if you’re not ready.”

You shook your head, biting back a small smirk, “N-No, I’m ready. I’ve just never been...naked in front of someone before.”

He smiled back at you softly before pressing a warm kiss to your cheek, “Don’t feel nervous. I have wanted to see how beautiful you are under your clothes for months. You’re _so_ sexy.”

He took your hand gently in his, leading you to the bedroom. As you approached the bed, he turned you so the back of your knees touched the edge of the bed. The man knelt down in front of you, placing gently kisses on your lower stomach as he unbuttoned your shorts. He slowly pulled the denim down your legs, tossing them away once they pooled at your feet. He pushed you lightly to get you to sit down at the edge of the bed. Slowly, you spread your legs before his began pressing warm kisses inside of your thighs. Looking up at you, his eyes searched yours for any indication to stop. You nodded you head, biting your bottom lip, giving him silent permission to continue his movements. He had never looked so gorgeous. Seeing him between your legs made you melt, wanting the man to be inside of you as soon as possible.

He slowly tucked his fingers under the waistband of your panties and peeled them down and off of your legs, leading to you feeling very cold and exposed. His eyes were trained to your center, which was currently dripping with need down red and wanting lips. You reached your hand down to thread it through his dirty-blonde hair, rubbing gently to encourage him to forward. Closing his eyes, his face inched closer to your pussy, inhaling deeply, “God, you are _so_ beautiful.”

His tongue traced in between your spread lips before he pressed a gentle and teasing kiss around your clit. Your thighs tensed as you whined high in your throat, tugging on his hair lightly. He removed his face before trailing his hands up your body, pushing closer so his chest was against your center, still kneeling before you at the edge of the bed. His hands found their way around your body, unhooking your bra. You let the straps fall down your shoulders before your nipples were exposed to the air. He placed his mouth over one of your exposed nipples, closing his eyes before biting gently down, sending a spark of pleasure down your body. You arched your back, pushing your breasts further into his face.

Biting your lip to contain the noises that were about to escape your lips, you trailed your hand down his back and then around his front, unbuttoning his jeans. After slowly pushing the zipper down, your hand froze, feeling warm skin against your hand. You couldn’t help the nervous giggle that escaped your mouth, “Commando? Really, Hopper?”

He chuckled lowly in his throat before pushing your chest down into the mattress, “You’re _such_ a brat.”

Standing up and hovering over you, he grabbed your neck and kissed you deeply. With one hand, he lifted your body up the bed, your head now resting on top of soft, white pillows as his large body hovered of your own. He removed his own jeans quickly, his thick cock springing free from the constraints of his pants. You broke this kiss to look down in between the both of you, letting out a moan when you saw just how thick and long he was, his member already swollen and leaking at the head.

He trailed his hand gently down your body before settling it in between your legs. He ran his thick digit down your center before dipping it in slightly between your lips to gather your wetness on his finger. He dragged it back up to your clit before circling it teasingly. Trying to ignore your nerves, you shut your eyes and arched your neck into the pillows. The feeling of his thick and large fingers against you felt so foreign to you; you didn’t want him to stop.

Gently, he inserted his index finger into you and began to rub gently circles over your clit with his thumb. Letting out a deep grown, you stuttered out, “O-Oh my god, _Hopper_. Your fingers are _so_ fucking big. _Shit_.”

“Think you can take another one?” he asking, working his finger in and out of you at a glacial pace, planting sloppy kisses across your chest.

You nodded your head quickly, spreading your legs further open. Your body tensed when he slid another large finger alongside his own, “Shit, baby. You’re so fucking tight.”

You let out a moan at the name, not having any control as you sobbed out, “C-Call me that again.”

“ _Baby_?” he asked with a devilish grin. “You like it when I call you baby girl? Huh?”

You moaned high in your throat as you nodded your head quickly, feeling your tight walls clench around his two fingers, your pussy gathering more and more wetness every time that he said the word.

“You know what I like?” he asked, sucking a bruise into your collarbone. “I like it when my baby girl gets all wet for me and my cock.”

You whimpered, lifting both of your hands to cover your reddened face in embarrassment, “Fuck, da- _hmm_.”

You quickly shut your mouth as soon as you felt the word try to escape your lips. The pace of his fingers quickened, sliding a third finger inside. You had never felt this full in your life, your nerves tightening in your stomach at the thought of taking his cock inside of you.

His ears perked up as a smile spread across his face, “What were you about to say, baby girl?”

“N-Nothing,” you said, shaking your head as sobs of pleasure escaped your mouth. Biting your lip, you began to thrust your hips up to meet the thrusts of his fingers.

“Don’t lie, baby,” he whispered. “Daddy doesn’t like it when you lie.”

You practically screamed, feeling yourself close to the edge.

He brushed against your g-spot aggressively as he grunted, “You like it when daddy fingers your tight, virgin pussy? Like it when I fuck your cunt with my fingers, baby girl?”

You nodded your head, the familiar heat pooling low in your stomach as your growled low, “Oh fuck! You gotta stop before I come. I’m gonna come.”

He quickly removed his fingers, causing you to wince at the empty feeling. He reached over to his nightstand before grabbing a condom. Looking down between you both, your lips parted as you saw him place the rubber over his thick head and down his shaft. He rested his arms on either side of you before he began to slowly push the tip of his cock inside of your opening.

“Let me know if it hurts, okay?” he said, concern flooding his eyes before you nodded in response. You rested your hands on his biceps, pressing your head against his forehead as he began to push inside of you.

You let out a sharp gasp as he slowly eased himself inside of your heat, your walls clenching down impossibly tight around him. He let out a low growl, resisting the urge to slam into you. You began to feel tears prickle the corners of your eyes as he bottomed out. The searing pain that came from between your legs shot up your body, causing you to tremble and whimper lightly. You had never felt anything so large inside of you, the stretch of his cock feeling like it was about to rip you in half.

You let out a slow breath, a tear rolling down your cheek. He looked at your face and his eyes filled with panic, “Are you okay? Did I hurt you? Do you need me to stop?”

“N-No,” you whispered. “Just...wait a minute. Please.”

He nodded, his face appearing pained as he held himself impossibly still. You reached your hand up to cup his face before pressing a chaste kiss to his parted lips. He gently traced his thumb around your clit, trying to turn your pain into pleasure. The pain soon began to transform into a dull fire, pleasure shooting up your legs. You slowly nodded your head against him, leading him to breathe heavily through his nose as he began to slide out of you slowly.

“Fuck,” he hissed, pushing himself in as his thumb never left your bud. “I’ve never felt something so tight, Jesus Christ.”

You tossed your head back as the feeling of his cock became more and more pleasurable with each drag against your walls. Placing your palms against his pecs, you lightly scratched the chest hair that sprinkled his chest, “Oh my god, Hop.”

“Are you okay?” he asked, slightly concerned. The care and gentleness radiating off of the man above you sent warmth to your chest and butterflies in your stomach.

“I’m okay,” you said with a grin, pressing a gentle kiss on his chest.

“You feel so good, baby,” he sobbed. “I don’t think I’m gonna last much longer. A-Are you close?”

You bit your lip as the pace of his hips began to pick up. He licked the pad of his thumb before returning it down to your clit, rubbing furiously in circles. You gasped loudly, sparks of intense pleasure shooting up your spins, “Shit! Yeah, I’m s-so close.”

He leaned down to whisper into your ear, “Come for me, baby girl. I want to feel you come all over my cock. Can you do that for daddy?”

“Fuck!” you screamed. “I’m gonna come, daddy. Oh fuck, you feel so good.”

“Come for me,” he growled, his hips pistoning into you as your eyes rolled back into your head.

Your mouth opened in a silent scream as you felt yourself come around Hopper’s cock, clenching around him and locking him in place. His eyes widened and a primal look of lust flooded his eyes.

“F-fuck, baby, I’m gonna come!” he grunted before feeling his body spasm.

Your hips rocked together, feeling the closest you had ever felt to another person. You had never felt this good before, and you never wanted to stop. Soon, your breathing returned to a normal rhythm. Looking up at him, you couldn’t help but giggle as you pictured how much of a mess you looked like; your hair was out of place, your forehead was damp with sweat, and your limbs laid strewn on the bed. He looked up at you with a shakey breath, pushing the hair out of your face before kissing your lips sweetly. He slowly pulled himself out of you, causing you to hiss at how empty you felt without him inside of you. Collapsing at your side, he ripped off the condom and tossed it into the trash.

You turned to him with a dopey grin on your face, “That was...wow.”

“Yeah,” he chuckled, pulling a blanket up and over the both of your bodies. He cupped your cheek and placed a kiss on the tip of your nose before looking at you with playful eyes, “So...daddy, huh?”

“Oh my god,” you groaned, cheeks heating up with embarrassment.

“Hey,” he laughed low in his check. “It was hot.”

You pushed his chest with a laugh, “But so so embarrassing.”

You cuddled into the warmth of his chest as he wrapped his arms around you, making you feel warm and safe surrounded by his body.

“How do you feel?” he whispered into your hair.

“I’m okay,” you said with a smile. “Better than okay, actually.”

“Good,” he said before pressing a kiss to your hairline. “Next time, it will even better.”

Looking up at him with a hopeful glint in your eyes, “Next time?”

“Well,” he said with a smug look. “I’m not letting you get away that easily, brat.”


End file.
